Ethyl bromodifluoroacetate

Ethyl bromodifluoroacetate
Names
IUPAC name
Ethyl 2-bromo-2,2-difluoroacetate
Systematic IUPAC name
Ethyl 2,2-dibromo-2-fluoro-acetate
Other names
Difluorobromoacetic acid ethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.517 Edit this at Wikidata
EC Number
  • 211-567-0
UNII
  • InChI=1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
    Key: IRSJDVYTJUCXRV-UHFFFAOYSA-N
  • InChI=1/C4H5Br2FO2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
  • BrC(Br)(F)C(=O)OCC
Properties
F2BrCHCO2CH2CH3
Molar mass 202.983 g·mol−1
Appearance Colorless to slightly yellow liquid
Density 1.583 g/mL
Boiling point 82 °C (180 °F; 355 K) pressure is at 33 torr
Vapor pressure 1.36 mmHg at 25°C
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethyl bromodifluoroacetate is an ester with the chemical formula F2BrCH−CO2CH2CH3. It can be used to introduce the CF2 group when synthesising chemical compounds. It is a colorless to yellow liquid. It is an ethyl ester of bromodifluoroacetic acid.

Formation

Ethyl fluorosulfonoxydifluoroacetate can react with sodium bromide (NaBr) to produce ethyl bromodifluoroacetate. And this reaction could happen in the solvent sulfolane. The reactions takes 12 hours at 100 °C with a yield of 31%.

Reactions

Ethyl bromodifluoroacetate, and other similar compounds containing a CF2 units can be generated using the Reformatsky reagent with aldehydes and ketones. This yields 2,2-difluoro-3-hydroxy esters. Also ethyl bromdifluoroacetate is considered to be a good compound in generation of compounds and for testing with other organic compounds like lactones, imines and other amino acids.[2]

References

  1. ^ datasheet, Santa Cruz Biotechnology, 2012
  2. ^ Sato, Kazuyuki; Tamura, Misato; Tamoto, Kei; Omote, Masaaki; Ando, Akira; Kumadaki, Itsumaro (2000). "Michael-type Reaction of Ethyl Bromodifluoroacetate with α,β-Unsaturated Carbonyl Compounds in the Presence of Copper Powder" (PDF). Chemical and Pharmaceutical Bulletin. 48 (7): 1023–1025. doi:10.1248/cpb.48.1023. PMID 10923834.